NPASS Compound

Structure

CID158756 OpenBabel06191715532D 25 26 0 0 1 0 0 0 0 0999 V2000 -4.5493 -2.0255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5279 -2.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2319 -2.5772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0050 0.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2129 -0.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2618 1.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 -1.8563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7089 -4.1789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0594 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8061 -1.3563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1211 -3.3698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2673 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 -1.7518 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1266 -3.4744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7035 -4.0743 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1083 2.5962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7199 -4.3879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -2.6654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 2 0 0 0 0 3 13 2 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 11 2 0 0 0 0 6 14 1 0 0 0 0 7 11 1 0 0 0 0 7 15 1 0 0 0 0 8 14 2 0 0 0 0 9 12 1 0 0 0 0 9 20 1 0 0 0 0 10 14 1 0 0 0 0 10 21 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 1 0 0 0 16 8 1 1 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 17 13 1 6 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.16
Volume:	356.99
LogP:	0.414
LogD:	1.244
LogS:	-2.891
# Rotatable Bonds:	5
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.455
Synthetic Accessibility Score:	4.862
Fsp3:	0.474
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.936
MDCK Permeability:	6.000372377457097e-05
Pgp-inhibitor:	0.062
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.884
20% Bioavailability (F20%):	0.587
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	73.03900146484375%
Volume Distribution (VD):	0.377
Pgp-substrate:	28.666746139526367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.079
CYP1A2-substrate:	0.053
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.176
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.237
CYP3A4-substrate:	0.192

ADMET: Excretion

Clearance (CL):	4.967
Half-life (T1/2):	0.907

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.345
Drug-inuced Liver Injury (DILI):	0.918
AMES Toxicity:	0.288
Rat Oral Acute Toxicity:	0.709
Maximum Recommended Daily Dose:	0.343
Skin Sensitization:	0.836
Carcinogencity:	0.38
Eye Corrosion:	0.02
Eye Irritation:	0.109
Respiratory Toxicity:	0.868

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC158756

Natural Product ID:	NPC158756
*Common Name:**	Onopordopicrin
IUPAC Name:	[(3aR,4S,6Z,10E,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
Synonyms:	Onopordopicrin
Standard InCHIKey:	NOZAJYKZMCFNFG-DGKKXOEVSA-N
Standard InCHI:	InChI=1S/C19H24O6/c1-11-5-4-6-14(10-21)8-16-17(13(3)19(23)25-16)15(7-11)24-18(22)12(2)9-20/h5,8,15-17,20-21H,2-4,6-7,9-10H2,1H3/b11-5-,14-8+/t15-,16+,17+/m0/s1
SMILES:	OC/C/1=C/[C@H]2OC(=O)C(=C)[C@@H]2[C@H](C/C(=CCC1)/C)OC(=O)C(=C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522604
PubChem CID:	6440861
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12232319]
NPO27695	Centaurea sonchifolia	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1624943]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22208890]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	fruit	n.a.	PMID[22396124]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO12423	Onopordum alexandrinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31199638]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12423	Onopordum alexandrinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25117	Onopordum algeriense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17280	Onopordum illyricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17280	Onopordum illyricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25117	Onopordum algeriense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12423	Onopordum alexandrinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27695	Centaurea sonchifolia	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
IC50	3

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	EC50	=	0.85	ug.mL-1	PMID[523648]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	13740.42	nM	PMID[523649]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[523649]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	13730.0	nM	PMID[523649]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC158756 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	1186
0.2-0.3	5118
0.3-0.4	12273
0.4-0.5	12875
0.5-0.6	6730
0.6-0.7	3275
0.7-0.8	867
0.8-0.85	85
0.85-0.9	55
0.9-0.95	34
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC470755
0.975	High Similarity	NPC469910
0.962	High Similarity	NPC169575
0.962	High Similarity	NPC40746
0.962	High Similarity	NPC473390
0.962	High Similarity	NPC131669
0.9615	High Similarity	NPC24417
0.9512	High Similarity	NPC476803
0.9512	High Similarity	NPC475819
0.9512	High Similarity	NPC476805
0.95	High Similarity	NPC476804
0.9494	High Similarity	NPC229825
0.9383	High Similarity	NPC255307
0.9359	High Similarity	NPC98557
0.9359	High Similarity	NPC167881
0.9286	High Similarity	NPC474232
0.9268	High Similarity	NPC475461
0.9268	High Similarity	NPC305475
0.9259	High Similarity	NPC114979
0.9259	High Similarity	NPC96259
0.9259	High Similarity	NPC141193
0.9259	High Similarity	NPC191476
0.9231	High Similarity	NPC471465
0.9231	High Similarity	NPC196653
0.9136	High Similarity	NPC59097
0.9125	High Similarity	NPC52861
0.9103	High Similarity	NPC141789
0.9103	High Similarity	NPC171204
0.9103	High Similarity	NPC7563
0.9103	High Similarity	NPC320630
0.9103	High Similarity	NPC476028
0.9103	High Similarity	NPC116177
0.8987	High Similarity	NPC93763
0.8987	High Similarity	NPC108816
0.8974	High Similarity	NPC68819
0.8902	High Similarity	NPC116543
0.8875	High Similarity	NPC270126
0.8864	High Similarity	NPC477922
0.8864	High Similarity	NPC471142
0.8851	High Similarity	NPC475302
0.8837	High Similarity	NPC475855
0.8837	High Similarity	NPC469368
0.8824	High Similarity	NPC473715
0.881	High Similarity	NPC150755
0.8765	High Similarity	NPC281132
0.8764	High Similarity	NPC477921
0.8764	High Similarity	NPC230800
0.875	High Similarity	NPC267231
0.8736	High Similarity	NPC473321
0.869	High Similarity	NPC165162
0.8636	High Similarity	NPC288240
0.8636	High Similarity	NPC295204
0.8636	High Similarity	NPC125674
0.8636	High Similarity	NPC228451
0.8636	High Similarity	NPC162205
0.8636	High Similarity	NPC273579
0.8636	High Similarity	NPC475838
0.8625	High Similarity	NPC97516
0.8625	High Similarity	NPC474760
0.8621	High Similarity	NPC144133
0.8621	High Similarity	NPC179394
0.8621	High Similarity	NPC473619
0.859	High Similarity	NPC295633
0.859	High Similarity	NPC58956
0.859	High Similarity	NPC269206
0.8556	High Similarity	NPC473859
0.8539	High Similarity	NPC474247
0.8506	High Similarity	NPC474032
0.8488	Intermediate Similarity	NPC266957
0.8481	Intermediate Similarity	NPC140287
0.8481	Intermediate Similarity	NPC476355
0.8481	Intermediate Similarity	NPC48641
0.8478	Intermediate Similarity	NPC288876
0.8471	Intermediate Similarity	NPC261380
0.8471	Intermediate Similarity	NPC21469
0.8462	Intermediate Similarity	NPC163003
0.8444	Intermediate Similarity	NPC475659
0.8427	Intermediate Similarity	NPC469645
0.8427	Intermediate Similarity	NPC469692
0.8415	Intermediate Similarity	NPC89128
0.8415	Intermediate Similarity	NPC19841
0.8391	Intermediate Similarity	NPC287089
0.8372	Intermediate Similarity	NPC469483
0.837	Intermediate Similarity	NPC471144
0.8352	Intermediate Similarity	NPC279621
0.8333	Intermediate Similarity	NPC121825
0.8333	Intermediate Similarity	NPC85772
0.8333	Intermediate Similarity	NPC89555
0.8333	Intermediate Similarity	NPC57405
0.8333	Intermediate Similarity	NPC303942
0.8295	Intermediate Similarity	NPC206001
0.8295	Intermediate Similarity	NPC218927
0.828	Intermediate Similarity	NPC475949
0.8272	Intermediate Similarity	NPC123360
0.8272	Intermediate Similarity	NPC235906
0.825	Intermediate Similarity	NPC476590
0.825	Intermediate Similarity	NPC114727
0.8235	Intermediate Similarity	NPC250315
0.8222	Intermediate Similarity	NPC475912
0.8214	Intermediate Similarity	NPC301477
0.8214	Intermediate Similarity	NPC141810
0.8214	Intermediate Similarity	NPC281949
0.8214	Intermediate Similarity	NPC25684
0.8202	Intermediate Similarity	NPC129419
0.8193	Intermediate Similarity	NPC470244
0.8193	Intermediate Similarity	NPC470239
0.8182	Intermediate Similarity	NPC136879
0.8182	Intermediate Similarity	NPC477302
0.8172	Intermediate Similarity	NPC141191
0.8161	Intermediate Similarity	NPC261721
0.8161	Intermediate Similarity	NPC50637
0.8152	Intermediate Similarity	NPC306041
0.8148	Intermediate Similarity	NPC155587
0.8118	Intermediate Similarity	NPC474252
0.8111	Intermediate Similarity	NPC261607
0.8111	Intermediate Similarity	NPC111114
0.8111	Intermediate Similarity	NPC300312
0.8105	Intermediate Similarity	NPC471148
0.809	Intermediate Similarity	NPC295312
0.809	Intermediate Similarity	NPC268298
0.8068	Intermediate Similarity	NPC160138
0.8068	Intermediate Similarity	NPC72513
0.8065	Intermediate Similarity	NPC471462
0.8065	Intermediate Similarity	NPC169205
0.8043	Intermediate Similarity	NPC471141
0.8043	Intermediate Similarity	NPC14961
0.8043	Intermediate Similarity	NPC270013
0.8043	Intermediate Similarity	NPC36954
0.8043	Intermediate Similarity	NPC304886
0.8023	Intermediate Similarity	NPC475947
0.8023	Intermediate Similarity	NPC318468
0.8023	Intermediate Similarity	NPC474703
0.8022	Intermediate Similarity	NPC165383
0.8	Intermediate Similarity	NPC71533
0.8	Intermediate Similarity	NPC106510
0.8	Intermediate Similarity	NPC470241
0.8	Intermediate Similarity	NPC128733
0.8	Intermediate Similarity	NPC325031
0.8	Intermediate Similarity	NPC185141
0.8	Intermediate Similarity	NPC46998
0.8	Intermediate Similarity	NPC129665
0.8	Intermediate Similarity	NPC164598
0.8	Intermediate Similarity	NPC110443
0.8	Intermediate Similarity	NPC474339
0.8	Intermediate Similarity	NPC133907
0.7978	Intermediate Similarity	NPC202672
0.7978	Intermediate Similarity	NPC260343
0.7976	Intermediate Similarity	NPC475210
0.7976	Intermediate Similarity	NPC617
0.7976	Intermediate Similarity	NPC178277
0.7957	Intermediate Similarity	NPC185553
0.7957	Intermediate Similarity	NPC476315
0.7952	Intermediate Similarity	NPC476794
0.7952	Intermediate Similarity	NPC470240
0.7949	Intermediate Similarity	NPC194871
0.7935	Intermediate Similarity	NPC140543
0.7935	Intermediate Similarity	NPC474035
0.7935	Intermediate Similarity	NPC471147
0.7935	Intermediate Similarity	NPC474338
0.7935	Intermediate Similarity	NPC81386
0.7935	Intermediate Similarity	NPC469632
0.7935	Intermediate Similarity	NPC167219
0.7917	Intermediate Similarity	NPC149371
0.7912	Intermediate Similarity	NPC184463
0.7912	Intermediate Similarity	NPC30515
0.7907	Intermediate Similarity	NPC11383
0.7907	Intermediate Similarity	NPC474959
0.7907	Intermediate Similarity	NPC475046
0.7907	Intermediate Similarity	NPC310450
0.7889	Intermediate Similarity	NPC166919
0.7875	Intermediate Similarity	NPC67183
0.7857	Intermediate Similarity	NPC127526
0.7849	Intermediate Similarity	NPC275960
0.7849	Intermediate Similarity	NPC90121
0.7849	Intermediate Similarity	NPC193645
0.7849	Intermediate Similarity	NPC48803
0.7841	Intermediate Similarity	NPC125290
0.7826	Intermediate Similarity	NPC179746
0.7826	Intermediate Similarity	NPC212486
0.7826	Intermediate Similarity	NPC476300
0.7826	Intermediate Similarity	NPC81419
0.7816	Intermediate Similarity	NPC229799
0.7816	Intermediate Similarity	NPC284472
0.7816	Intermediate Similarity	NPC286770
0.7812	Intermediate Similarity	NPC47880
0.7812	Intermediate Similarity	NPC244456
0.7812	Intermediate Similarity	NPC469657
0.7802	Intermediate Similarity	NPC51004
0.7802	Intermediate Similarity	NPC473448
0.7802	Intermediate Similarity	NPC474761
0.7802	Intermediate Similarity	NPC476004
0.7802	Intermediate Similarity	NPC473455
0.7802	Intermediate Similarity	NPC19087
0.7791	Intermediate Similarity	NPC471325
0.7789	Intermediate Similarity	NPC473326
0.7789	Intermediate Similarity	NPC187268
0.7778	Intermediate Similarity	NPC477513
0.7766	Intermediate Similarity	NPC17585
0.7765	Intermediate Similarity	NPC99651
0.7755	Intermediate Similarity	NPC220964

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC158756 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1783
0.2-0.3	3790
0.3-0.4	2319
0.4-0.5	711
0.5-0.6	321
0.6-0.7	45
0.7-0.8	22
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7849	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD5785	Approved
0.764	Intermediate Similarity	NPD5363	Approved
0.7614	Intermediate Similarity	NPD7154	Phase 3
0.75	Intermediate Similarity	NPD4270	Approved
0.75	Intermediate Similarity	NPD4269	Approved
0.7471	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4252	Approved
0.7444	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4225	Approved
0.7419	Intermediate Similarity	NPD6698	Approved
0.7419	Intermediate Similarity	NPD46	Approved
0.7363	Intermediate Similarity	NPD5786	Approved
0.734	Intermediate Similarity	NPD7983	Approved
0.7255	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4268	Approved
0.7241	Intermediate Similarity	NPD4271	Approved
0.7222	Intermediate Similarity	NPD5362	Discontinued
0.7212	Intermediate Similarity	NPD6371	Approved
0.7191	Intermediate Similarity	NPD5369	Approved
0.7174	Intermediate Similarity	NPD4249	Approved
0.7097	Intermediate Similarity	NPD4250	Approved
0.7097	Intermediate Similarity	NPD4251	Approved
0.7083	Intermediate Similarity	NPD5779	Approved
0.7083	Intermediate Similarity	NPD5778	Approved
0.7079	Intermediate Similarity	NPD4822	Approved
0.7079	Intermediate Similarity	NPD4819	Approved
0.7079	Intermediate Similarity	NPD4821	Approved
0.7079	Intermediate Similarity	NPD4820	Approved
0.7065	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1695	Approved
0.6947	Remote Similarity	NPD5370	Suspended
0.6923	Remote Similarity	NPD5209	Approved
0.6923	Remote Similarity	NPD6435	Approved
0.6875	Remote Similarity	NPD7838	Discovery
0.6869	Remote Similarity	NPD7839	Suspended
0.6854	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6101	Approved
0.6739	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5368	Approved
0.6702	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD5332	Approved
0.6633	Remote Similarity	NPD7637	Suspended
0.6633	Remote Similarity	NPD6411	Approved
0.663	Remote Similarity	NPD4790	Discontinued
0.6596	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4756	Discovery
0.6542	Remote Similarity	NPD6686	Approved
0.6435	Remote Similarity	NPD8516	Approved
0.6435	Remote Similarity	NPD8515	Approved
0.6435	Remote Similarity	NPD8513	Phase 3
0.6435	Remote Similarity	NPD8517	Approved
0.6429	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6399	Phase 3
0.6346	Remote Similarity	NPD7639	Approved
0.6346	Remote Similarity	NPD7640	Approved
0.6341	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8039	Approved
0.6306	Remote Similarity	NPD6053	Discontinued
0.6286	Remote Similarity	NPD5344	Discontinued
0.6279	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7638	Approved
0.6167	Remote Similarity	NPD8074	Phase 3
0.6122	Remote Similarity	NPD6422	Discontinued
0.6118	Remote Similarity	NPD3197	Phase 1
0.6071	Remote Similarity	NPD2204	Approved
0.6058	Remote Similarity	NPD4228	Discovery
0.6038	Remote Similarity	NPD6648	Approved
0.6019	Remote Similarity	NPD6647	Phase 2
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD5697	Approved
0.5979	Remote Similarity	NPD6110	Phase 1
0.5962	Remote Similarity	NPD5695	Phase 3
0.5957	Remote Similarity	NPD3732	Approved
0.5946	Remote Similarity	NPD6899	Approved
0.5946	Remote Similarity	NPD6881	Approved
0.5943	Remote Similarity	NPD5696	Approved
0.5929	Remote Similarity	NPD6649	Approved
0.5929	Remote Similarity	NPD6650	Approved
0.5917	Remote Similarity	NPD7829	Approved
0.5917	Remote Similarity	NPD7830	Approved
0.5917	Remote Similarity	NPD7642	Approved
0.5909	Remote Similarity	NPD5739	Approved
0.5909	Remote Similarity	NPD7128	Approved
0.5909	Remote Similarity	NPD6402	Approved
0.5909	Remote Similarity	NPD6675	Approved
0.5905	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6373	Approved
0.5893	Remote Similarity	NPD6014	Approved
0.5893	Remote Similarity	NPD6013	Approved
0.5893	Remote Similarity	NPD6012	Approved
0.5893	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6372	Approved
0.5882	Remote Similarity	NPD368	Approved
0.5876	Remote Similarity	NPD3667	Approved
0.5875	Remote Similarity	NPD3172	Approved
0.5865	Remote Similarity	NPD7748	Approved
0.5856	Remote Similarity	NPD5701	Approved
0.5841	Remote Similarity	NPD6421	Discontinued
0.5841	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6883	Approved
0.5841	Remote Similarity	NPD7102	Approved
0.5841	Remote Similarity	NPD7290	Approved
0.5825	Remote Similarity	NPD7515	Phase 2
0.5823	Remote Similarity	NPD6927	Phase 3
0.582	Remote Similarity	NPD8273	Phase 1
0.5814	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD7500	Approved
0.5804	Remote Similarity	NPD7320	Approved
0.5804	Remote Similarity	NPD6011	Approved
0.5802	Remote Similarity	NPD3194	Approved
0.5802	Remote Similarity	NPD3195	Phase 2
0.5802	Remote Similarity	NPD3196	Approved
0.5802	Remote Similarity	NPD4266	Approved
0.58	Remote Similarity	NPD6684	Approved
0.58	Remote Similarity	NPD6409	Approved
0.58	Remote Similarity	NPD7334	Approved
0.58	Remote Similarity	NPD3618	Phase 1
0.58	Remote Similarity	NPD7521	Approved
0.58	Remote Similarity	NPD7146	Approved
0.58	Remote Similarity	NPD5330	Approved
0.5795	Remote Similarity	NPD7331	Phase 2
0.5795	Remote Similarity	NPD3704	Approved
0.5789	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6847	Approved
0.5789	Remote Similarity	NPD8130	Phase 1
0.5789	Remote Similarity	NPD6617	Approved
0.5789	Remote Similarity	NPD6869	Approved
0.578	Remote Similarity	NPD7632	Discontinued
0.578	Remote Similarity	NPD5211	Phase 2
0.5758	Remote Similarity	NPD3133	Approved
0.5758	Remote Similarity	NPD3665	Phase 1
0.5758	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD3666	Approved
0.5758	Remote Similarity	NPD4786	Approved
0.5752	Remote Similarity	NPD6413	Approved
0.575	Remote Similarity	NPD8444	Approved
0.5739	Remote Similarity	NPD6882	Approved
0.5739	Remote Similarity	NPD8297	Approved
0.5736	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD342	Phase 1
0.5727	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7900	Approved
0.5714	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD2067	Discontinued
0.5691	Remote Similarity	NPD8451	Approved
0.5686	Remote Similarity	NPD6903	Approved
0.5686	Remote Similarity	NPD5737	Approved
0.5686	Remote Similarity	NPD6672	Approved
0.5686	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.568	Remote Similarity	NPD7319	Approved
0.5676	Remote Similarity	NPD5141	Approved
0.5673	Remote Similarity	NPD8034	Phase 2
0.5673	Remote Similarity	NPD8035	Phase 2
0.5673	Remote Similarity	NPD5693	Phase 1
0.5673	Remote Similarity	NPD5281	Approved
0.5673	Remote Similarity	NPD5284	Approved
0.567	Remote Similarity	NPD4695	Discontinued
0.5667	Remote Similarity	NPD6319	Approved
0.5664	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.566	Remote Similarity	NPD4629	Approved
0.566	Remote Similarity	NPD5210	Approved
0.5657	Remote Similarity	NPD6695	Phase 3
0.5652	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD8448	Approved
0.5644	Remote Similarity	NPD5279	Phase 3
0.5644	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD4753	Phase 2
0.563	Remote Similarity	NPD7641	Discontinued
0.5625	Remote Similarity	NPD6008	Approved
0.5625	Remote Similarity	NPD5048	Discontinued
0.5619	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.561	Remote Similarity	NPD8342	Approved
0.561	Remote Similarity	NPD8341	Approved
0.561	Remote Similarity	NPD8299	Approved
0.561	Remote Similarity	NPD8340	Approved
0.561	Remote Similarity	NPD7492	Approved
0.56	Remote Similarity	NPD5766	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data